At least the third song on this list about a guy mulling over romantic gestures he wishes he’d made to his former love, and the most traditional among those songs. You could easily imagine this one being a minor classic by a 60’s or 70’s legend, so close is its replication of that style. – Dan Milliken

My hard-and-fast rule for Toby Keith: The sadder he is, the happier the listening experience tends to be. He’s all kinds of sad in this snapshot of post-divorce melancholia, reflecting on everything from unfair custody protocol to the greater motions of the universe. Even a gratuitous Sting cameo can’t detract from the single’s gloomy grandeur. – DM

Toby Keith is also funny, though. What’s a man to do? Sobering up ain’t all that it’s cracked up to be from is perspective. Ever since he’s done so, his wife has been taking advantage of his increased functionality by giving him honey-do lists that he wasn’t ably tackling pre-sobriety. It’s enough to drive a man to drink. – Leeann Ward

Every once and awhile an artist delivers a song so powerful that it seems to shatter all divides in its genre. A tribute to both the late Keith Whitley and Gill’s late brother, “Go Rest High On That Mountain” pairs deeply spiritual lyrics with a tender, emotion-soaked performance. The combination is magic. – TS

A good power ballad shot to greatness by its artists’ striking chemistry – palpable, fiery and so very genuine. More than just a hit single, “It’s Your Love” represents the moment in country music history at which we were introduced to one of its definitive couples. – TS

An earnest, soulful confession of love. It’s hard to ignore the fact that it leans more in the adult-contemporary direction than that of anything else, but when a song is this moving, it’s also hard to care. – TS

In an unusual tact for Mr. Brooks, he forgoes melodrama in order to allow the natural drama of pining for a lost love to speak for itself. The dialed down performance works in the service of the song, as the sadness appropriately penetrates through. – LW

Some of the best songs from AKUS play on the home life that’s sacrificed by following the musical dream. Krauss remembers how she used to laugh at songs about the lonely traveling life, but she’s not laughing now. – KC

A man makes a soaring yet understated plea for his lover to let go of her past love. The song is made sadder by the touch of resignation in Wariner’s performance, which suggests the man knows he’s making his plea in vain. – TS

A whole song about deciding whether or not to go all the way with one’s movie date. McCready gives a fantastically entertaining performance, speak-singing her lines with a a bold campiness that most other gals wouldn’t dare. – DM

Ten years before “You Belong With Me” made its splash, McCann set her sights on the same demographic with a song just as relatable, vibrant and passionate. That the song lacks Taylor Swift’s sharp perspective is perhaps what makes it such a great record: there’s something so pure about McCann’s fully unapologetic, headfirst fall into love. – TS

Chesnutt makes a phone call to an old love that could be construed as creepy, pathetic or terribly sad – take your pick. I’m going with a mixture of all three, with a pinch of selfishness thrown in. Either way, “I Just Wanted You to Know” is a memorable slice of the-one-that-got-away reality.- TS

In the twenty years that passed since the release of this song, the path to success in the music industry has morphed into something that looks very different than it used to. Unlike that of Bobby in the song, these days an artist’s journey can come in all shapes and forms, sometimes abrupt and sometimes completely unprecedented.

Think what you want about this paradigm shift, but here’s what I believe: regardless of how you shoot to the top, the only way you’ll achieve longevity and, most importantly, respect in country music is if you share the fire in Bobby’s eyes. This soul-stirring hunger and unshakable passion is the heart of “I’m Gonna Be Somebody” and the reason it remains a timeless classic. Here’s to hoping – and I’m optimistic – our modern artists are made of the same stuff. – TS

22 Comments on 400 Greatest Singles of the Nineties: #250-#226

Absolutely NO recollection of the Robert Ellis Orrall number so I’ll have to go look that one up.

I may be in the minority here, but I’ve never particularly cared for Gill’s “Go Rest High”.

And I love the Toby Keith/Sting duet! He’s one of those artists who frustrates me. Kind of like Trace Adkins who I can love on a song like “I’m Tryin'” or “Then They Do”, but hate more than anyone else on some of their other material. “You Ain’t Much Fun” isn’t quite as bad as “American Ride”, “She’s a Hottie”, “High Maintenance Woman”, etc., but it’s still not one I’d ever desire to hear again.

Nice to see Kim Richey represented here, and twice yet. I personally think she is underrated as a recording artist, and her music falls in that little crease between country and rock; but she is far better a singer than the public gives her credit for. And as a songwriter, she is way up there at or near the top (IMHO).

In the case of “What If I Do”–it is really quite a tragedy to listen to Mindy on that song, realize how good she was becoming at that time, and how utterly far she has personally fallen since then. And to demonstrate how much potential was lost, “What If I Do” is on the same 1997 album (IF I DON’T STAY THE NIGHT) where she bravely covers Linda Ronstadt’s 1970 country-rock classic “Long Long Time.”

I too am surprized to see Lila McCann on the list. I met her in 07 and she is sooooo nice. Her “Lila”album came out when I was 12 and everyone my age loved and owned it. She was, in my opinion, the Taylor Swift of my generation except she can sing. I hope to see “Down Came A Blackbird” on the list later. We used to sing that song on the bus ride home from school. Good times!!!!!!!

another interesting group of songs. I never heard the Mandy Barnett song. thanks. I like it. I didn’t know that B&D’s “My Maria” was a pop cover. I haven’t listened to pop radio in over 30 years.

My favorites here are the songs by Lee Roy Parnell, Billy Dean and Garth Brooks. In fact, checking the I-Tunes count on my MacBook, I’ve played “What She’s Doing Now” more than any other song by Garth.

Just seen Travis perform in my hometown last night and I gotta say he’s still got the fire, “I’m Gonna Be Somebody” was a real highlight of the set. Got to meet him as well, smaller guy than I thought.

One of my fave Garth songs. I also like that cd because it was right before Garth became “Garth” and his music lost so much, IMHO.

Really cool to see the Kim Richey shout-outs. One of my fave songwriters and when you see her live you think, “she wrote THAT?”.

I always really liked Vince’s “Go Rest High…” and whenever I’ve seen him perform it, especially at memorials, it never ceases to get to me. It’s just one of those songs that seems to have been written for a divine purpose.

Kenny Chesney: Don’t know the song but the cd cover in that little hat is worth the price of admission.

My first concert was Tim McGraw and Faith Hill, and one of the best moments was when they sang “It’s Your Love.” That song is such a classic. I love their heartfelt performances, and I love the prominent steel guitar as well.

I was a little surprised to see Lila McCann’s “With You” on this list. I like it, but I didn’t think it sounded like the kind of song that would get a spot on this list. It’s kind of like ear candy, but it’s tasty ear candy!

Robert Ellis Orral was a talented songwriter whose career as a performer never took off. I am not sure what his greatest success as a writer was but the #1 Shenandoah hit “Next To You, Next To Me” immediately comes to mind.

I’m glad to see that there’s someone else who doesn’t particularly care for Vince Gill’s “Go Rest High”. Bar bands in my area insist on resurrecting the song continuously

One of the things I’m noticing with this list thus far is that I like most of these songs but love very few of them. That wouldn’t be true for a rundown of the 50s,60s or 70s

There’s no doubt that “Go Rest High” has a great impact and it’s one of Vince’s career songs, but it’s not among my personal favorite Gill songs either. It’s never done anything for me for some reason.

I love the harmonies on “Go Rest High.” They really make the chorus soar the way that a song of this nature needs to.

But I’ve always found the opening verse awkward. “You were no stranger to the rain” is a clumsy way to point out it’s a tribute to Whitley, IMO, and it compromises the universality of the sentiment a bit for me.

Kenny Chesney in the 90’s may have had a “run-of-the-mill” 90’s sound, but man was he enjoyable to listen to. Not just a few singles worth of listenable, good material like Fall in Love or Me and You, but entire albums worth of good country. I wish for an album, hell a single, Kenny would rediscover his 90’s sound and allow us to hear Kenny Chesney, the talent, good, country artist.

Really pleased to see the Robert Ellis Orral song, that was always one of my favorites. Surprised that the Travis Tritt song didn’t make the T100, going to be very interested in seeing the rest of the list.

It’s a shame that Sting got relegated to a “gratuitous” cameo on Keith’s version, as Sting’s original version blows it out of the water, and is far more country to boot. I can’t listen to Keith’s version because of it.